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Oleamide

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Oleamide
Names
Preferred IUPAC name
(9Z)-Octadec-9-enamide
Other names
oleoyl-amide
Oleylamide
9-Octadecenamide
(Z)-9-Octadecenamide
9,10-Octadecenoamide
Oleic acid amide
Cis-9,10-octadecenoamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.550 Edit this at Wikidata
EC Number
  • 206-103-9
UNII
  • InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9- checkY
    Key: FATBGEAMYMYZAF-KTKRTIGZSA-N checkY
  • InChI=1/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9-
    Key: FATBGEAMYMYZAF-KTKRTIGZBR
  • O=C(N)CCCCCCC\C=C/CCCCCCCC
Properties
C18H35NO
Molar mass 281.484 g·mol−1
Appearance Creamy solid[1]
Density 0.879 g/cm3
Melting point 70 °C (158 °F; 343 K)<[2]
Boiling point > 200 °C (392 °F; 473 K)[1]
Insoluble[1]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
0
0
Flash point > 200 °C (392 °F; 473 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Oleamide is an organic compound with the formula CH3(CH2)7CH=CH(CH2)7CONH2.[3] It is the amide derived from the fatty acid oleic acid. It is a colorless waxy solid and occurs in nature. Sometimes labeled as a fatty acid primary amide (FAPA), it is biosynthesized from N-oleoylglycine.[4]

Biochemical and medical aspects

[edit]

In terms of natural occurrence, oleamide was first detected in human plasma. It was later shown to accumulate in the cerebrospinal fluid during sleep deprivation and induces sleep in animals.[4][5]

It has been considered as a treatment for mood and sleep disorders, as well as cannabinoid-regulated depression.[6][7]

In terms of its sleep inducing effects, it is speculated that oleamide interacts with multiple neurotransmitter systems.[8][9] Some in-vitro studies show that cis-oleamide is an agonist for the cannabinoid receptor CB-1 with an affinity around 8 micromolar.[10] However, given oleamide's relatively low affinity for CB-1 and uncertainty about the concentration and biological role of oleamide in-vivo, it has been argued that it is premature to classify oleamide as an endocannabinoid.[11] At larger doses oleamide can lower the body temperature of mice by about 2 degrees, with the effect lasting about two hours.[9] The mechanism for this remains unknown.[9]

Oleamide has been found to enhance PPARα-dependent increase in doublecortin, a marker of neurogenesis in the hippocampus[12]

Oleamide is rapidly metabolized by fatty acid amide hydrolase (FAAH), the same enzyme that metabolizes anandamide.[13] It has been postulated that some effects of oleamide are caused by increased concentrations of anandamide brought about through the inhibition of FAAH.[9]

It has been claimed that oleamide increases the activity of choline acetyltransferase, an enzyme that is critical in the production of acetylcholine.[14]

Other occurrences

[edit]

Oleamide has been found in Ziziphus jujuba, also known as Jujube fruit.[14]

Synthetic oleamide has a variety of industrial uses, including as a lubricant.[15]

Oleamide was found to be leaching out of polypropylene plastics in laboratory experiments, affecting experimental results.[16] Since polypropylene is used in a wide number of food containers such as those for yogurt, the problem is being studied.[17]

Oleamide is "one of the most frequent non-cannabinoid ingredients associated with Spice products."[18] Analysis of 44 products synthetic cannabinoid revealed oleamide in 7 of the products tested.[19]

See also

[edit]

References

[edit]
  1. ^ a b c d Oleamide at chemicalland21.com
  2. ^ "(9Z)-9-Octadecenamide | C18H35NO | ChemSpider".
  3. ^ "Oleamide".
  4. ^ a b McKinney, Michele K.; Cravatt, Benjamin F. (June 2005). "Structure and Function of Fatty Acid Amide Hydrolase". Annual Review of Biochemistry. 74 (1): 411–432. doi:10.1146/annurev.biochem.74.082803.133450. PMID 15952893. S2CID 23571858.
  5. ^ Cravatt, B.; Prospero-Garcia, O; Siuzdak, G; Gilula, N.; Henriksen, S.; Boger, D.; Lerner, R. (9 June 1995). "Chemical characterization of a family of brain lipids that induce sleep". Science. 268 (5216): 1506–1509. Bibcode:1995Sci...268.1506C. doi:10.1126/science.7770779. PMID 7770779. S2CID 32070839.
  6. ^ Methods of treating anxiety and mood disorders with oleamide – US Patent 6359010 Archived 2011-06-12 at the Wayback Machine
  7. ^ Mechoulam, Raphael; Fride, Ester; Hanu, Lumir; Sheskin, Tzviel; Bisogno, Tiziana; Di Marzo, Vincenzo; Bayewitch, Michael; Vogel, Zvi (September 1997). "Anandamide may mediate sleep induction". Nature. 389 (6646): 25–26. Bibcode:1997Natur.389R..25M. doi:10.1038/37891. PMID 9288961. S2CID 26371103.
  8. ^ Fedorova, I; Hashimoto, A; Fecik, RA; Hedrick, MP; Hanus, LO; Boger, DL; Rice, KC; Basile, AS (October 2001). "Behavioral evidence for the interaction of oleamide with multiple neurotransmitter systems". The Journal of Pharmacology and Experimental Therapeutics. 299 (1): 332–42. PMID 11561096.
  9. ^ a b c d Hiley, C. Robin; Hoi, Pui Man (13 April 2007). "Oleamide: A Fatty Acid Amide Signaling Molecule in the Cardiovascular System?: OLEAMIDE". Cardiovascular Drug Reviews. 25 (1): 46–60. doi:10.1111/j.1527-3466.2007.00004.x. PMID 17445087.
  10. ^ Leggett, JD; Aspley, S; Beckett, SR; D'Antona, AM; Kendall, DA; Kendall, DA (January 2004). "Oleamide is a selective endogenous agonist of rat and human CB1 cannabinoid receptors". British Journal of Pharmacology. 141 (2): 253–62. doi:10.1038/sj.bjp.0705607. PMC 1574194. PMID 14707029.
  11. ^ Fowler, Christopher J (January 2004). "Oleamide: a member of the endocannabinoid family?: Commentary". British Journal of Pharmacology. 141 (2): 195–196. doi:10.1038/sj.bjp.0705608. PMC 1574195. PMID 14691053.
  12. ^ Roy, Avik; Kundu, Madhuchhanda; Chakrabarti, Sudipta; Patel, Dhruv R; Pahan, Kalipada (December 2021). "Oleamide, a Sleep-Inducing Supplement, Upregulates Doublecortin in Hippocampal Progenitor Cells via PPARα". J Alzheimers Dis. 84 (4): 1747–1762. doi:10.3233/JAD-215124. PMC 10075226. PMID 34744082.
  13. ^ Maurelli, Stefano; Bisogno, Tiziana; De Petrocellis, Luciano; Di Luccia, Aldo; Marino, Gennaro; Di Marzo, Vincenzo (11 December 1995). "Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma 'anandamide amidohydrolase'". FEBS Letters. 377 (1): 82–86. Bibcode:1995FEBSL.377...82M. doi:10.1016/0014-5793(95)01311-3. PMID 8543025. S2CID 7461775.
  14. ^ a b Heo, Ho-Jin; Park, Young-June; Suh, Young-Min; Choi, Soo-Jung; Kim, Mi-Jeong; Cho, Hong-Yon; Chang, Yun-Jeong; Hong, Bumshik; Kim, Hye-Kyung; Kim, Eunki; Kim, Chang-Ju; Kim, Byung-Gee; Shin, Dong-Hoon (January 2003). "Effects of Oleamide on Choline Acetyltransferase and Cognitive Activities". Bioscience, Biotechnology, and Biochemistry. 67 (6): 1284–1291. doi:10.1271/bbb.67.1284. PMID 12843655.
  15. ^ Surfactants : Westco Oleamide a Slip Agent In Polyethylene Films Archived January 27, 2007, at the Wayback Machine
  16. ^ McDonald, G. R.; Hudson, A. L.; Dunn, S. M. J.; You, H.; Baker, G. B.; Whittal, R. M.; Martin, J. W.; Jha, A.; Edmondson, D. E.; Holt, A. (7 November 2008). "Bioactive Contaminants Leach from Disposable Laboratory Plasticware". Science. 322 (5903): 917. Bibcode:2008Sci...322..917M. doi:10.1126/science.1162395. PMID 18988846. S2CID 35526901.
  17. ^ Mittelstaedt, Martin (6 November 2008). "Researchers Raise Alarm After Chemical Leak Found In Common Plastic". Globe and Mail. Retrieved 10 June 2013.
  18. ^ Fattore, Liana; Fratta, Walter (21 September 2011). "Beyond THC: The New Generation of Cannabinoid Designer Drugs". Frontiers in Behavioral Neuroscience. 5: 60. doi:10.3389/fnbeh.2011.00060. PMC 3187647. PMID 22007163.
  19. ^ Uchiyama, Nahoko; Kikura-Hanajiri, Ruri; Ogata, Jun; Goda, Yukihiro (May 2010). "Chemical analysis of synthetic cannabinoids as designer drugs in herbal products". Forensic Science International. 198 (1–3): 31–38. doi:10.1016/j.forsciint.2010.01.004. PMID 20117892.
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